Add the sugar, water, and cinnamon to a small sauce pan and bring to a boil.
Reduce heat to a simmer and cook, stirring occasionally, for 5-10 minutes or until the sugar has completely dissolved.
Remove from the heat and stir in the vanilla.
Cool completely before using. Store in a mason jar in the fridge for up to 2 weeks.
To rim the glass:
Pour cranberry juice onto a rimmed plate.
Add the sugar and cinnamon onto a second plate and stir gently to combine.
Dip the rim of the glass first in the cranberry juice and then in the cinnamon and sugar, rolling the rim of the glass through the sugar to coat.
To make the cocktail:
In your cocktail shaker combine cranberry juice, orange liquor, vodka, and cinnamon syrup. Add ice and shake well to combine.
Strain the mixture into your rimmed glass and top with sparkling water and a sprig of fresh rosemary.
Notes
For a sweeter drink, you may use Sprite in place of the sparkling water. We like Cointreau or Grand Mariner for the orange liqueur, but you can use any brand you like. Our homemade cinnamon syrup is easy enough to make, but you can also purchase cinnamon syrup at many specialty stores or online.